Scotland produced a battling performance at Hampden to earn a draw against group-leaders Italy.
Kenny Miller put Walter Smith's side ahead after 13 minutes when he nodded in Paul Hartley's teasing cross.
Substitute Fabio Grosso equalised after 76 minutes when he fired home from close-range after Craig Gordon had made a superb one-handed save from a corner.
However, Christian Dailly's second-half yellow card means he will miss the next match against Norway.
Scotland lined up at Hampden having not beaten Italy since 1965, when a John Greig goal separated the two sides.
However, the class of 2005 put themselves under pressure after only a minute when Nigel Quashie brought down former Rangers midfielder Gennaro Gattuso with a clumsy challenge.
Francesco Totti's free-kick fell perfectly into the path of the unmarked Cristian Zaccardo at the back post, but his left-foot strike was brilliantly blocked by Gordon.
Christian Vieri gave Gordon another test in the ninth minute after beating Andy Webster in the air, but the youngster held his low drive comfortably.
However, Scotland opened the scoring four minutes later after carving out their first real chance with a well-worked move.
Graham Alexander found Darren Fletcher in space and the midfielder checked back and stroked the ball out wide to Hartley, who whipped in an inviting cross from the right-hand side.
Miller got across Zaccardo and headed the ball powerfully past Angelo Peruzzi from six yards.
Italy carved out a great opportunity to move level in the 37th minute after Scotland had failed to clear a Totti free-kick.
The Roma striker's cross skimmed the head of De Rossi, which forced Vincenzo Iaquinta to stretch for the ball and send it over the bar.
In the 44th minute, Vieri went down in the box under the challenge of David Weir, but the referee waved play on.
Weir became the last-gasp hero of the first half when he blocked Vieri's volley after a clever ball over the top from Totti.
Scotland could have been punished after the restart when Totti was allowed too much time on the ball as he raced towards goal.
Fortunately for Walter Smith's side, the Italian playmaker could only pull his shot wide from 19 yards.
Moments later, Dailly was booked for a foolish foul on Totti that rules him out of the midweek clash with Norway.
On the hour mark, Alexander knocked his back-pass straight to Totti, who then ran through on goal and picked out Vieri at the back post.
Unbelievably, the Milan striker put the ball over from close range with Gordon struggling to make up ground across his goalline and most of the Italians held their heads in their hands.
The inevitable equaliser came after 76 minutes courtesy of second-half substitute Grosso.
Gordon made a superb save to keep Fletcher's header from Totti's corner ending up in the back of his own net, but Grosso pounced at the back post to fire into the net.
The point for Scotland keeps their World Cup hopes hanging in the balance, with three points a necessity from their next match against Norway.
Scotland: Gordon, McNamara, Webster, Weir, Alexander, Fletcher, Dailly, Ferguson, Hartley, Quashie (McCann 66), Miller (Beattie 76).
Subs Not Used: Douglas, Caldwell, McFadden, Murray, O'Neil.
Booked: Ferguson, Miller, Dailly, Beattie.
Goal: Miller 13.
Italy: Peruzzi, Zaccardo (Grosso 45), Cannavaro, Nesta, Zambrotta, De Rossi (Camoranesi 60), Gattuso, Pirlo, Totti, Vieri, Iaquinta (Toni 71).
Subs Not Used: De Sanctis, Materazzi, Barone, Del Piero.
Booked: Zambrotta, De Rossi, Totti.
Goal: Grosso 76.
Ref: Michel Lubos (Slovakia).